Benzenesulfonyl chloride, 4-chloro-3-nitro- → 4-Chloro-3-nitrobenzenesulfonic acid-n-(1-methylpiperidin-4-yl)-n-methylamide
反応式
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH3:9])[CH2:4][CH2:3]1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>N1C=CC=CC=1>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]([CH3:9])[S:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[C:12]([N+:21]([O-:23])=[O:22])[CH:13]=2)(=[O:18])=[O:19])[CH2:4][CH2:3]1参加物
4
実験手順
To a solution of 2.2 mL (15 mmol) of 1-methyl-4-methylaminopiperidine in 60 mL pyridine, 3.8 g (15 mmol) of 4-chloro-3-nitrobenzenesulfonic acid chloride were added, in batches, whilst cooling with ice. The mixture was then stirred for two hours with cooling, then evaporated to dryness, the residue was mixed with about 50 mL of water and made alkaline with concentrated ammonia whilst stirring vigorously. The crude product precipitated was suction filtered and purified by column chromatography (250 g silica gel, eluant: dichloromethane with 1.5% ethanol). Yield: 1.6 g (31% of theory), C13H18ClN3O4S (347.8); Rf value: 0.19 (silica gel; dichloromethane/ethanol=19:1).